You need someone to help you with your approach, engage in playful rounds of verbal sparring so that you seem witty, and chat up any friends your target has in tow to free you and your intended up for a love connection. Someone to be the Goose to your Maverick, if you will. But what are the rules of such a set up? This is where things can get tricky.
A friend recently sent me an email detailing her distaste for the way a man behaved while she was serving as wingwoman one night. She said the gentleman attempting to win over her friend virtually ignored her – the cardinal sin men can commit in a social setting. Be nice to the friend, be nice to the friend, be nice to the friend – always, and under all circumstances.
Because after all, when you walk away, if you’ve rubbed the wrong way the one who will have her ear on the ride home, you’ve just shot yourself down and all of that hard work was for naught. So here are a few behavioral guidelines for those chatting up someone with a wingman in tow, as well as for the wingman (or woman) him or herself. It’s not rocket science, but it needs to be said.
Be inclusive, not exclusive - If the person you’re talking to has a friend (or friends) with them, as I said, make sure to engage them in conversation as well. Or, at least make eye contact while you’re talking to the one you’re really interested in, so that they don’t feel like human furniture. Eye contact or nodding when they talk is just as effective an interaction. I can’t emphasize this enough.
Even if you are underwhelmed by said friend, this will make the friend think you have manners, and possibly rally in your favor later on if he or she thinks you’re particularly funny or charming. If there is a momentary lull in conversation, ask how they know each other, chat up the friend about what she does for work – whatever, just keep the exchange going as long as possible to gain an opportunity to showcase your personality.
Smile - There is nothing as disarming as smiling at someone. People should do it more often, in my opinion. So, if you’re talking to a woman you’re into, make steady eye contact, smile (not in a goofy, cartoon-ish way though) and be as relaxed as possible. It’s just a conversation, don’t over-think it.
For those serving as wingman/woman - It becomes clear fairly quickly who the intended target is, so if it’s established that it’s your friend’s affections that are being sought, you have some responsibilities as well. If you seem to like the person who just approached (or at least don’t abhor them instantly), you would do well to help him or her out. It’s good karma.
If there is an awkward silence, jump in and ask a question, like, “So, what does a (fill in the blank job) do exactly?” *Note, obviously if the person has an easy job, like a dentist, that’s pretty self-explanatory. Don’t inquire unless you want to look slightly challenged in the smarts department.
Or you could talk up your friend if you think that he or she could use some help closing the deal. Casually bring up something impressive about them, or if he or she is particularly funny take a cue from earlier and do the whole witty banter thing. Verbally tag-teaming your friends makes you both look approachable and reminds us all of our own friendships, which helps put people at ease.
But whatever you do, try to avoid cutting the poor person at the knees and forcing them to walk away with a bruised ego and shattered confidence. It takes guts to approach someone, after all, and that type of bravery should never be scoffed at or insulted – unless the person approaching is particularly lecherous or annoying.
In that case, the wingman should fake an asthma attack or say something to your friend like, “Hey isn’t that your girlfriend (or boyfriend) over there?” and then point to the most intimidating-looking person in the room. Then make a hasty escape.
It shouldn’t be that hard to meet people, we do it every day in various circumstances. It is, however, hard to meet people of substance, worth keeping around. So if you’re on the prowl or just keeping a buddy company, remember that some rules of decorum apply. And if you can’t be helpful or straighten up and fly right, perhaps you’re better off staying home.